30 days in Oregon Itinerary

The city of Hood River is the seat of Hood River County, Oregon, United States. Explore Hood River's surroundings by going to Government Camp (Timberline Lodge and Ski Area, Trillium Lake, &more). There's lots more to do: identify plant and animal life at Columbia River Gorge National Scenic Area, hike along Historic Columbia River Highway State Trail, learn about all things military at Fort Dalles Museum and Anderson Homestead, and take a memorable drive along Hood River County Fruit Loop.

To see traveler tips, more things to do, ratings, and tourist information, use the Hood River road trip app.

Boston to Hood River is an approximately 8-hour flight. You can also drive; or do a combination of bus and train. The time zone difference moving from Eastern Standard Time (EST) to Pacific Standard Time (PST) is minus 3 hours. In September in Hood River, expect temperatures between 71°F during the day and 57°F at night. Finish your sightseeing early on the 4th (Mon) to allow enough time to fly to Bend.

An old logging town at the crux of the high desert and ponderosa pine forest, Bend melds a love of the outdoors with cosmopolitan flair.

Explore the numerous day-trip ideas around Bend: Sisters (Sahalie and Koosah Falls & McKenzie Pass-Santiam Pass loop), Wildland Firefighters Monument (in Prineville) and Dee Wright Observatory (in Blue River). And it doesn't end there: immerse yourself in nature at Smith Rock State Park, see Off-Road Tours, see the interesting displays at High Desert Museum, and hike along Pilot Butte State Scenic Viewpoint.

To find photos, more things to do, ratings, and tourist information, read our Bend online route planner.

You can fly from Hood River to Bend in 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Hood River in September, Bend is slightly colder at night with lows of 44°F. Wrap up your sightseeing on the 9th (Sat) early enough to drive to Crater Lake National Park.

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.

Go for a jaunt from Crater Lake National Park to Prospect to see National Creek Falls about 30 minutes away. Spend the 10th (Sun) exploring nature at Crater Lake National Park. There's much more to do: explore and take pictures at Rim Dr, hike along Sun Notch Trail, admire the sheer force of Whitehorse Falls, and cruise along Rogue-Umpqua Scenic Byway.

To see reviews and more tourist information, refer to the Crater Lake National Park trip planner.

You can drive from Bend to Crater Lake National Park in 2.5 hours. Another option is to do a combination of bus and taxi. In September, Crater Lake National Park is a bit warmer than Bend - with highs of 83°F and lows of 53°F. Finish your sightseeing early on the 13th (Wed) to allow enough time to drive to Ashland.

Ashland is a city in Jackson County, in the State of Oregon. Explore the numerous day-trip ideas around Ashland: Medford (Rogue River & Natural Bridge Loop), Grants Pass (Wildlife Images - Rehabilitation & Education Center & Reinhart Volunteer Park) and Pacific Crest National Scenic Trail (in Dufur). There's lots more to do: relax and float downstream with a rafting and tubing tour, stroll around Lithia Park, and see a show at Oregon Shakespeare Festival.

To see maps, photos, reviews, and other tourist information, read Ashland attractions planner.

Getting from Crater Lake National Park to Ashland by car takes about 2 hours. Other options: do a combination of taxi and bus. Expect a daytime high around 83°F in September, and nighttime lows around 53°F. Finish up your sightseeing early on the 16th (Sat) so you can go by car to Newport.

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.

You'll find plenty of places to visit near Newport: Florence (Sea Lion Caves & Heceta Head Lighthouse) and Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Yachats coastline). And it doesn't end there: get up close and personal with brilliant marine life at Oregon Coast Aquarium, admire the majestic nature at South Beach State Park, walk around Whale Park, and take a memorable drive along Oregon Coast Hwy.

For other places to visit, photos, where to stay, and more tourist information, use the Newport online holiday maker.

Getting from Ashland to Newport by car takes about 5 hours. Other options: do a combination of flight and bus; or take a bus. Traveling from Ashland in September, expect nights in Newport to be about the same, around 50°F, while days are little chillier, around 64°F. Finish your sightseeing early on the 20th (Wed) to allow enough time to drive to Astoria.

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.

You'll find plenty of places to visit near Astoria: Manzanita Beach (in Manzanita), Cannon Beach (Hug Point State Park, Haystack Rock, &more) and Nehalem Bay State Park (in Nehalem). There's still lots to do: stroll through Astoria Column, pause for some photo ops at Seaside Beach Lewis and Clark Monument, see the interesting displays at Seaside Inverted Experience, and explore the striking landscape of Fort Clatsop National Memorial.

For other places to visit, where to stay, photos, and tourist information, use the Astoria day trip app.

Drive from Newport to Astoria in 3.5 hours. Alternatively, you can take a bus. In September in Astoria, expect temperatures between 69°F during the day and 52°F at night. Wrap up your sightseeing on the 24th (Sun) early enough to drive to Portland.

A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.

Explore the numerous day-trip ideas around Portland: Multnomah Falls (in Bridal Veil) and McMinnville (Evergreen Aviation & Space Museum & R Stuart & Co.). Dedicate the 27th (Wed) to wine at some of the top wineries in the area. And it doesn't end there: take in nature's colorful creations at Portland Japanese Garden, hunt for treasures at Portland Saturday Market, learn about wildlife with up-close encounters at Oregon Zoo, and don't miss a visit to Pittock Mansion.

To see photos, maps, where to stay, and more tourist information, go to the Portland travel route builder site.

You can drive from Astoria to Portland in 2 hours. Another option is to take a bus. While traveling from Astoria, expect a bit warmer days and about the same nights in Portland, ranging from highs of 76°F to lows of 55°F. Wrap up your sightseeing by early afternoon on the 30th (Sat) to allow enough time to fly back home.